Technology Process of (R)-3,4-Dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-1H-2-benzopyran-1-one
There total 8 articles about (R)-3,4-Dihydro-8-hydroxy-6,7-dimethoxy-3-methyl-1H-2-benzopyran-1-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: D-Prolin; Nitrosobenzene / acetonitrile / 24 h / -20 °C
1.2: 0.5 h / 0 °C
1.3: 12 h / 20 °C
2.1: p-toluenesulfonyl chloride; di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C
2.2: 5 h / 0 - 20 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 0 - 20 °C
3.2: 0 °C
4.1: boron trichloride / dichloromethane; n-heptane / 2 h / -10 °C
With
dmap; boron trichloride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; Nitrosobenzene; p-toluenesulfonyl chloride; D-Prolin;
In
n-heptane; dichloromethane; acetonitrile;
3.1: |Pictet-Spengler Synthesis;
DOI:10.1016/j.tet.2020.131524
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: dichloromethane / 12 h / 20 °C
2.1: hydrogen; palladium 10% on activated carbon / methanol / 10 h / 20 °C / 5171.62 Torr
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -78 °C
4.1: D-Prolin; Nitrosobenzene / acetonitrile / 24 h / -20 °C
4.2: 0.5 h / 0 °C
4.3: 12 h / 20 °C
5.1: p-toluenesulfonyl chloride; di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C
5.2: 5 h / 0 - 20 °C
6.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 0 - 20 °C
6.2: 0 °C
7.1: boron trichloride / dichloromethane; n-heptane / 2 h / -10 °C
With
dmap; palladium 10% on activated carbon; hydrogen; boron trichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triethylamine; Nitrosobenzene; p-toluenesulfonyl chloride; D-Prolin;
In
methanol; n-heptane; dichloromethane; toluene; acetonitrile;
1.1: |Wittig Olefination / 6.1: |Pictet-Spengler Synthesis;
DOI:10.1016/j.tet.2020.131524
